Potassium Carbonate → HCID 67065454, compound

HRID 1967113Notes

Reaction equation

HRID 1967113 reaction equation
Br[C:2]1[O:6][CH:5]=[C:4]([C:7]([NH:9][C@@H:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[O:8])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:47]2[N:51]([CH3:52])[N:50]=[CH:49][CH:48]=2)OC1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:22]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[CH2:11][C@@H:10]([NH:9][C:7]([C:4]1[CH:3]=[C:2]([C:47]2[N:51]([CH3:52])[N:50]=[CH:49][CH:48]=2)[O:6][CH:5]=1)=[O:8])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole2×HCID 67065485HCID 67065485, compound

Product 1

HCID 67065454HCID 67065454, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-furancarboxamide (400 mg, 0.77 mmol) in dioxane/H2O (5:1, 50 mL) was added K2CO3 (0.32 g, 2.3 mmol), tetrakistriphenylphosphine Pd(0) (20 mg, 40 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (0.19 g, 0.92 mmol). The reaction mixture was heated to 75° C. in a sealed tube. After 5 h, additional tetrakistriphenylphosphine Pd(0) (20 mg, 40 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (0.19 g, 0.92 mmol) were added. After 8 h, the reaction solution was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organics were dried (Na2SO4), concentrated under vacuum and purified on silica gel (hexanes/EtOAc, 1:2) to give the title compound (200 mg, 50%) as white solid: LCMS (ES) m/z=523.

Workup

  1. waitAfter 8 h
  2. customthe reaction solution was then partitioned between H2O-DCM
  3. washthe aqueous phase was washed several times with DCM
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. custompurified on silica gel (hexanes/EtOAc, 1:2)

Sources & evidence

ORD record
ord-6d3d50c3dadc493a9579cb69bb8c2b02
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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